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Organic Chemistry - Naming

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21 views26 pages

Organic Chemistry - Naming

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bnoitaestrella
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Naming Organic Compounds

Chemistry HL
NOMENCLATURE:
IUPAC SYSTEM

• IUPAC (International Union of


Pure and Applied Chemistry) is
an international, non-
governmental organization
known for its system of
nomenclature now recognized
world wide.
• IUPAC uses the size of the
molecules and the functional
groups present to logically name
compounds.
Classification of Hydrocarbons

Hydrocarbons are made up of only hydrogen and carbon.

3
Alkanes

Alkanes have the general formula CnH2n+2 where n = 1,2,3,…


• only single covalent bonds
• saturated hydrocarbons because they contain the
maximum number of hydrogen atoms that can bond with the
number of carbon atoms in the molecule

CH4 C2H6 C3H8

methane ethane propane

4
Structural isomers are molecules that have the same
molecular formula but different structures. 5
24.1

How many structural isomers can be identified for pentane,


C5H12?

6
24.1
Solution The first step is to write the straight-chain structure:
H H H H H

H C C C C C H

H H H H H

n-pentane
(b.p. 36.1 oC)
The second structure, by necessity, must be a branched chain:
H CH3 H H

H C C C C H

H H H H

2-methylbutane
(b.p. 27.9 oC)
7
24.1
Yet another branched-chain structure is possible:
H CH3 H

H C C C H

H CH3 H

2, 2-dimethylpropane
(b.p. 9.5 oC)

We can draw no other structure for an alkane having the


molecular formula C5H12. Thus, pentane has three structural
isomers, in which the numbers of carbon and hydrogen atoms
remain unchanged despite the differences in structure.

8
Physical Properties of Some Alkanes

9
Alkane Nomenclature

1. The parent name of the hydrocarbon is that given to the


longest continuous chain of carbon atoms in the molecule.
CH3 4-methylheptane
CH3 CH2 CH2 CH CH2 CH2 CH3 heptane
1 2 3 4 5 6 7

2. An alkane less one hydrogen


atom is an alkyl group.

CH4 methane

CH3 methyl
10
Alkane Nomenclature

3. When one or more hydrogen atoms are replaced by other


groups, the name of the compound must indicate the
locations of carbon atoms where replacements are made.
Number in the direction that gives the smaller numbers for
the locations of the branches.
CH3

CH3 CH CH2 CH2 CH3


1 2 3 4 5
2-methylpentane CH3

CH3 CH2 CH2 CH CH3


1 2 3 4 5

4-methylpentane
11
Alkane Nomenclature

4. Use prefixes di-, tri-, tetra-, when there is more than one
alkyl branch of the same kind.
CH3 CH3

CH3 CH CH CH2 CH2 CH3


1 2 3 4 5 6

2,3-dimethylhexane
CH3

CH3 CH2 C CH2 CH2 CH3


1 2 3 4 5 6
CH3

3,3-dimethylhexane 12
Alkane Nomenclature

5. Use previous rules for other types of substituents.

Br NO2

CH3 CH CH CH3
1 2 3 4
2-bromo-3-nitrobutane
Cl F

CH2 CH2 CH CH3


1 2 3 4

1-chloro-3-fluorobutane

13
24.2

Give the IUPAC name of the following compound:

CH3 CH3

H3C C CH2 CH CH2 CH3

CH3

14
24.2

Solution The longest chain has six C atoms so the parent


compound is called hexane. Note that there are two methyl
groups attached to carbon number 2 and one methyl group
attached to carbon number 4.
CH3 CH3
1 2 3 4 5 6
H3C C CH2 CH CH2 CH3

CH3

Therefore, we call the compound 2,2,4-trimethylhexane.

15
RULE 1: IDENTIFY THE LONGEST
STRAIGHT CHAIN OF CARBON ATOMS
This longest chain is the “stem”. Memorize these:
• Meth – 1
• Eth – 2
• Prop – 3
• But – 4
• Pent – 5
• Hex – 6
• Hept – 7
• Oct – 8
• Non – 9
• Dec -10
RULE 2: IDENTIFY THE FUNCTIONAL
GROUP
• The functional group will be a specific “suffix”
which replaces the –ane in the parent alkane.
RULE 3: • Substituent groups are given as the first part of the name
or are the prefix of the name.

IDENTIFY • Common substituents are: methyl-, ethyl-


propyl-, flouro- (-F), chloro- (-Cl), bromo- (-Br), iodo- (-I),
THE SIDE and amino- (NH2).
• Note that –NH2 can be a suffix or a prefix. Usually,
CHAINS OR when it is the only functional group, it will be the
suffix. If there are 2 or more functional groups, it will

SUBSTITUEN be a prefix as in amino acids.


• The position of the substituent group is given by a number

T GROUPS followed by a hyphen in front of its name showing the


carbon atom to which it is attached.
• If there are more than one substituent group of
the same kind, use the prefixes di-, tri-, tetra-
before the name.
• Always number the groups from the shortest end
of the parent carbon chain.
• If there is more than one type of substituent
group, they are put in alphabetical order.
Naming
alkenes
• The longest chain
must include the
double bond ( pi
bond)
Naming
alcohols
1. Select the longest continuous chain to which
the hydroxyl group is directly attached.
Change the name of the alkane
corresponding to the chain by dropping the
final -e and adding the suffix -ol.
2. Number the longest continuous carbon chain
so as to give the carbon atom bearing the
hydroxyl group the lower number. Indicate
the position of the hydroxyl group by using
this number as a locant.
3. Indicate the position of another substituent
as a prefix by using the numbers
corresponding to their positions along the
carbon chain
Naming
aldehyde
•Select the longest continuous chain to
which the hydroxyl group is directly
attached. Change the name of the
alkane corresponding to the chain by
dropping the final -e and adding the
suffix -al.
•Number the longest continuous carbon
chain so as to give the carbon atom
bearing the hydroxyl group the lower
number.
•Indicate the position of another
substituent as a prefix by using the
numbers corresponding to their
positions along the carbon chain
Naming
ketones
•Select the longest continuous chain to
which the hydroxyl group is directly
attached. Change the name of the alkane
corresponding to the chain by dropping
the final -e and adding the suffix -one
•Number the longest continuous carbon
chain so as to give the carbon atom
bearing the hydroxyl group the lower
number. Indicate the position of the
hydroxyl group by using this number as a
locant.
•Indicate the position of another
substituent as a prefix by using the
numbers corresponding to their positions
along the carbon chain
Naming
carboxyllic acids
•Select the longest continuous chain to
which the hydroxyl group is directly
attached. Change the name of the
alkane corresponding to the chain by
dropping the final -e and adding the
suffix –ic acid.
•Number the longest continuous carbon
chain so as to give the carbon atom
bearing the hydroxyl group the lower
number.
•Indicate the position of another
substituent as a prefix by using the
numbers corresponding to their
positions along the carbon chain
Naming esters
• Esters are named as alkyl caboxylate
• Since esters are made from a reaction
between alcohol and carboxyllic acid
• The alklyl part of the name comes from the
alcohol
• The carboxylate part of the name comes from
the carboxylic acid
Naming
esters

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